Pentane → (2-(4-Chlorophenyl)-1-(phenylsulfonyl)-1H-imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanone

HRID 63233

Reaction equation

HRID 63233 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:10]=[CH:11][N:12]=2)=[CH:4][CH:3]=1.C([Li])(C)(C)C.CCCCC.[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH:40]=[C:41]([O:45][CH3:46])[C:42]=1[O:43][CH3:44])[C:37](Cl)=[O:38]>C1COCC1.C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([S:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:10]=[C:11]([C:37]([C:36]3[CH:40]=[C:41]([O:45][CH3:46])[C:42]([O:43][CH3:44])=[C:34]([O:33][CH3:32])[CH:35]=3)=[O:38])[N:12]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8003PentaneHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 497885002-(4-Chlorophenyl)-1-(phenylsulfonyl)-1H-imidazoleHCID 178418306HCID 178418306, compound

Product 1

HCID 49788802(2-(4-Chlorophenyl)-1-(phenylsulfonyl)-1H-imidazol-4-yl)(3,4,5-trimethoxyphenyl)methanoneYield 36.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 2-(4-chlorophenyl)-1-(phenylsulfonyl)-1H-imidazole (10f) (6.0 mmol) in anhydrous THF (30 mL) at −78° C. was added 1.7 M tert-butyllithium in pentane (5.3 mL, 9.0 mmol) and stirred for 10 min. 3,4,5-Trimethoxybenzoyl chloride (7.2 mmol) was added at −78° C. and stirred for overnight. The reaction mixture was diluted with 100 mL of saturated NaHCO3 solution (aqueous) and extracted by ethyl acetate (200 mL). The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography (hexane:ethyl acetate 4:1) to give a white solid. Yield: 36.8%; 1H NMR (500 MHz, CDCl3) δ 8.05 (d, J=7.5 Hz, 2H), 7.77 (t, J=7.5 Hz, 1H), 7.62 (t, J=8.0 Hz, 2H), 7.48 (s, 1H), 7.44 (d, J=9.0 Hz, 2H), 7.39 (d, J=8.5 Hz, 2H), 7.37 (s, 2H). MS (ESI): calculated for C25H21ClN2O6S, 512.1. found 513.1 [M+H]+.

Workup

  1. stirringstirred for overnight
  2. extractionextracted by ethyl acetate (200 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (hexane:ethyl acetate 4:1)
  6. customto give a white solid

Sources & evidence

ORD record
ord-e16d5251861942d0865ec6ca7d3f8d39
Source dataset
uspto-grants-2016_09
Patent number
US09447049B2

Linked notes

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